This proposal involves studies for the synthesis of the antitumor agent antibiotic 593 A. This antibiotic is a naturally-occurring nitrogen mustard and structurally is the piperazinedione of a new amino acid, streptolutine. Key methods to be studied in the synthesis are (1) coupling of an optically active dialkylcopper lithium reagent, derived from (S)-malic acid, with appropriate alpha, beta-dehydroamino acids, (2) introduction of the beta-amino function by Curtius reaction or by Michael addition, (3) introduction of chirality by stereospecific reduction of a dehydroamino acid, and (4) formation of the piperidine ring by cyclization involving an amine function. Analogs will be prepared that have sulfur introduced into the molecule in place of the piperidyl nitrogen.